Papilledema is a high-risk cause of vision changes in the Emergency Department (ED) and a critical physical examination finding because of its close association with etiologies that may progress to vision loss or death. Syphilis is a rare infectious cause of papilledema, with scarce case reports published showing its ability to develop such sequela. We present a case of a 35-year-old male with a past medical history of newly diagnosed HIV who originally presented to the ED with a rash and rapidly worsening visional changes. While in the ED, the patient developed a brief syncopal episode and acute vision loss, after which concern for increased intracranial pressure and possible opportunistic infection guided the clinicians to perform a bedside point of care ultrasound (POCUS) that confirmed bilateral papilledema. The patient ultimately had an expedited work-up that rendered a diagnosis of syphilitic papillitis and uveitis without associated neurosyphilis. With the growing incidence of syphilis in the US, we aim to shed light on the rare diagnosis of isolated ocular syphilis in hopes of increasing awareness of this potentially vision-threatening pathology. This case also serves as an important reminder of the utility of POCUS in working up undifferentiated visual complaints and concerns of papilledema.